Hawaii’s Most Luxurious Vacations Rentals
Sorted by most expensive per night and grouped by island.
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Maui:
1. Kai Ala
Kaanapali, Hawaii
This exquisite eleven thousand square foot Luxury Vacation home, on nearly a full private acre, and located directly on Kaanapali Beach is hotel-zoned as a beach-front luxury vacation home. Perfect for entertaining large groups of people with its 8 bedrooms and 9.5 baths…
10 Beds
9.5 Baths
8 Bedrooms
2. Garden Villa
Kaanapali, Hawaii
This 12 bedroom gem combines all four villas in building 2 of the Luana Garden Villas. 2 adjacent grounded villas and the 2 adjacent elevated villas directly above boast a combined 8000 sq ft of interior living area, perfect for that large special gathering…
12 Beds
14 Baths
12 Bedrooms
3. Lipoa Kahakai
Kihei, Hawaii
The courtyard is completely private, exclusive for the guests of Aloha Villas Resort. There is gated parking with 8 parking spaces, electronic gates to enter the courtyard, and surveillance cameras for your safety and security. Within the courtyard is a heated saltwater…
12 Beds
14 Baths
12 Bedrooms
4. Luana Garden
Kaanapali, Hawaii
This luxurious 9 bedroom gem combines two neighboring ground villas with an elevated neighbor directly above to create over 6000 sq ft of interior living area, perfectly suited to larger groups or families. Since you will be staying within the 38 beachfront acres…
9 Beds
9 Baths
9 Bedrooms
5. Honua Kai Resort
Kaanapali, Hawaii
Enjoy an effortless vacation with footstep access to Enclave Three’s pool, hot tub, and fire pit area, as well as a convenient location in very close proximity to the greater Honua Kai Resort amenities including the Hokulani deli, Duke’s Beach House…
9 Beds
9 Baths
9 Bedrooms
6. Kapalua Bay Villa
Kapalua, Hawaii
With over 2700 square feet of indoor living space and an additional 628 sq. ft. of outdoor relaxation, this villa will comfortably entertain a large gathering. Exotic hardwoods gleam in the sunshine streaming through the full-length windows and Nano doors and reflect…
3 Beds
3 Baths
3 Bedrooms
7. Honua Garden
Kaanapali, Hawaii
Enjoy an effortless vacation with footstep access to Enclave Three’s pool, hot tub, and fire pit area, as well as a convenient location in very close proximity to the greater Honua Kai Resort amenities including the Hokulani deli, Duke’s Beach House…
9 Beds
9 Baths
9 Bedrooms
8. Makena Garden
Makena, Hawaii
Makena Garden Estate is an upscale contemporary-styled 4,800 square foot 4.5 bedroom (King, King, King, Queen) 4 bath virtual oceanfront home with spectacular panoramic ocean views in the leeward sunnier Makena area on Maui Island…
9 Beds
9 Baths
9 Bedrooms
9. Maui Baby Beach
Lahaina, Hawaii
This is ‘Your Own Private Paradise’ on Maui. There is an additional studio villa with a full Kitchen and Bath. Recently installed is a new multi-zone air conditioning and cooling system for your use to keep you comfortable while you gaze out the 180-degree oc…
5 Beds
5 Baths
4 Bedrooms
10. Kapalua Ikena
Kapalua, Hawaii
Explore the beautiful artwork, vaulted ceilings, custom woodwork, and openness to the outdoors. Custom-built cabinetry and stainless steel appliances compliment the large granite island with seating. The separate dining room opens onto the lanai with Nano doors…
5 Beds
5 Baths
4 Bedrooms
11. Lahaina Moana
Lahaina, Hawaii
Welcome to Maui’s most desirable vacation home! Your own private mansion on the water in Lahaina (this home is partial oceanfront). This is currently the largest vacation rental in Hawaii in terms of both square footage and sleeping arrangements…
4 Beds
5 Baths
8 Bedrooms
12. Maui Kukuna
Spreckelsville, Maui
This private estate is spread over 2 ½ acres of prime beachfront in exclusive Spreckelsville, Maui, HI, containing stately palms, a variety of bamboos, and lush tropical plants. This gated property offers a secluded and protected launching beach, and spacious…
4 Beds
5 Baths
8 Bedrooms
13. Pacific View
Lahaina, Hawaii
Pacific View is nestled in the majestic West Maui Mountains, a vast area of lush valleys and steep cliffs. This lovely 5-acre estate is uniquely situated to capture all of the beautiful west Maui offers, yet just a short drive to the heart of historic Lahaina town…
8 Beds
5 Baths
6 Bedrooms
14. Maui Kukuna
Lahaina, Hawaii
We invite you to unwind at Paradise Cove, an oceanfront property located in Napili on the stunningly beautiful West shore of Maui. You, your family, and friends are sure to be pleased with this 3 bedroom plus office, 4.5 bathroom home, complete…
3 Beds
3.5 Baths
3 Bedrooms
15. Garuda Estate
Lahaina, Hawaii
We invite you to indulge in this magnificent 3,300 square foot villa nestled on the southwest shore of Maui. From the moment you arrive at the statue flanked entry, you’ll be in awe with views of the majestic blue ocean, and the Island of Lana’i in the distance…
3 Beds
3 Baths
3 Bedrooms